benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate

Base Information

• Chemical Name: benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate
• CAS No.: 173653-48-0
• Molecular Formula: C₂₁H₃₁NO₅
• Molecular Weight: 377.481

Synonyms:benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate

Chemical Property of benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate

Chemical Property:

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Technology Process of benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate

There total 4 articles about benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate (173653-47-9) + methyl iodide (74-88-4) → benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate (173653-48-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.43.1706

Reference yield: 34.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate (173653-47-9) → benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate (173653-48-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1248/cpb.43.1706

Reference yield:

Boc-L-Pro-H (69610-41-9,117625-90-8) → benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate (173653-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 34 percent / BF₃*OEt₂ / CH₂Cl₂

With boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.43.1706

upstream raw materials:

diazomethane

benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate

methyl iodide

benzyl proprionate

Downstream raw materials:

N-(tert-Butoxycarbonyl)-(9S,10R,11S)-iso-dolaproinyl-dolaphenine

(S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide

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